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Chlorendic anhydride/maleic anhydride compositions and method for preparing same

a technology of chlorendic anhydride and composition, which is applied in the preparation of carboxylic compounds, organic chemistry, chemistry apparatus and processes, etc., can solve the problems of inability to achieve the final reaction product, the unsatisfactory effect of color and flammability, and the inability to achieve the product form

Inactive Publication Date: 2005-08-18
VELSICOL CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention is about a new process for making a mixture of chlorendic and maleic anhydrides. This mixture is made by heating hexachlorocyclopentadiene in a reactor with agitation and the absence of liquid hydrocarbons and halohydrocarbons. Molten maleic anhydride is gradually added to the reaction mixture while maintaining it as a molten material, and the resulting mixture is cooled to form a solid mixture of chlorendic and maleic anhydrides. This new process results in a more efficient and effective mixture of anhydrides for use in polyester precursors. The resulting polyester precursors have improved properties and can be used in various applications."

Problems solved by technology

Even relatively minute amounts of these solvents can impart undesirable color and flammability to the final reaction product.
This form of product cannot be achieved using the solvent required as part of the prior art techniques for preparing chlorendic anhydride from the reactants of the present method.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0041] Eight hundred (800) parts of HCCPD were placed in a glass reactor equipped with heating means, a thermometer, a water-cooled condenser, a mechanically driven stirrer, an addition funnel equipped with means for heating the contents, a gas inlet tube extending to the bottom of the reactor and connected to a compressed air source, and a gas inlet providing a nitrogen atmosphere above the reactants.

[0042] With the gases flowing through both inlets, the HCCPD was heated to 160° C., at which time 373.9 parts of molten maleic anhydride were gradually added from the heated addition funnel. The temperature of the maleic anhydride in the funnel was 90° C. The maleic anhydride was added to the reactor at a rate of 6.2 grams per minute while the contents of the reactor were stirred and heated at 160° C.

[0043] Following completion of the MA addition, stirring and heating of the reaction mixture at 160° C. was continued for about 4 hours together with the flow of gases through both gas i...

example 2

[0045] This example describes 1) an alternative method for preparing the chlorendic anhydride / maleic anhydride mixtures of the present invention and 2) addition of a glycol to form a polyester precursor.

Step 1—Production of Crude Chlorendic Anhydride

[0046] One hundred and fifty (150) parts of HCCPD were placed in a glass reactor equipped with heating means, thermometer, water-cooled condenser, mechanically activated stirrer, a pressure-equalizing addition funnel equipped with a heating means, a gas inlet tube extending to the bottom of the reactor and connected to a compressed air source, and a gas inlet providing a nitrogen atmosphere above the reactants. Using a compressed air flow rate of 9.52 ml. / minute and a nitrogen flow rate of 90.48 ml. / minute the HCCPD was heated to 174° C., at which time 53.92 parts of molten MA were added from the heated addition funnel over a 90 minute period with stirring.

[0047] Heating of the reaction mixture was continued for an additional 30 to 4...

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Abstract

Mixtures of chlorendic anhydride and maleic anhydride that are completely free of liquid hydrocarbons and liquid halohydrocarbons without the need for any purification are novel and are prepared by reacting hexachlorocyclopentadiene with a stoichiometric excess of maleic anhydride in the absence of solvents. The process is useful for preparing other Diels-Alder reaction products from maleic anhydride.

Description

BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] This invention relates to mixtures of chlorendic anhydride and maleic anhydride. More particularly, this invention relates to those mixtures that are entirely free of organic solvents. This invention also provides a process for preparing chlorendic anhydride / maleic anhydride mixtures employing no materials other than the reactants, specifically hexachlorocyclopentadiene and maleic anhydride. This process does not require the liquid hydrocarbon associated with prior art methods for preparing these mixtures, thereby avoiding the associated problems of recovery and either disposal or recycling of the recovered hydrocarbon. [0003] The anhydride mixtures of this invention can be combined with one or more dihydric alcohols to prepare flame retardant polyesters. [0004] The present method is useful for preparing other Diels-Alder type reaction products of a conjugated cyclic diene with a cyclic alkene. One or both of the re...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C51/567C08G63/00C08G63/682C08G63/78
CPCC07C51/567C08G63/6826C08G63/78C07C61/29
Inventor MCCONNELL, WESLEY WAYNEKONDUBHOTLA, SUJATHAJOSHI, MAKARANDZIMMERMANN, ERICWITTENAUER, JOHNNETZEL, NEALSTANHOPE, BRUCEZHUKHOVYTSKYY, VLADIMIR
Owner VELSICOL CHEM CORP